2-Aminopyridine → HCID 19610850, compound

Participants

Reaction Steps

1.73 g (18 mmol, 1 eq) of 2-aminopyridine are added to a suspension of 5.00 g (18 mmol), 1 eq) of 2,3-dichloro-1,4-dihydro-1,4-dioxo-5-nitronaphthalene in 400 mL of ethanol. The mixture is brought to reflux for 5 h. After an orange precipitate appears, the reaction is allowed to cool to ambient temperature and the precipitate is filtered and purified on a flash column (support: silica 6-35 μm, h=45 cm, δ=16 cm; conditioning: heptane/ethyl acetate, 50/50; eluant: heptane/ethyl acetate, 50/50 to 70/30) to obtain 0.54 g of 6,11-dihydro-6,11-dioxo-7-nitronaphtho[2',3':4,5]imidazo[1,2-a]pyridine or 6,11-dihydro-6,11-dioxo-10-nitronaphtho[2',3':4,5]imidazo[1,2-a]pyridine, which after recrystallization in 1,2-dichlorobenzene produces 0.24 g of the expected product in the form of orange crystals.

Provenance & Evidence